Diphenylacetylene from the decomposition of 2,2-diphenyl-1-tosylazoethylene

Rosini, Goffredo; Cacchi, Sandro

doi:10.1021/jo00976a054

Cited by 11 publications

(2 citation statements)

References 3 publications

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“…Signals at 6 6.53 and 5.36 are assigned to the hydrogen atoms at C-6 and C-7, respectively; those at C-4a and C-7a appear as a multiplet at 6 5.14-5. 25.…”

Section: Results and Discussiionmentioning

confidence: 99%

“…1 6 1 8 s cm-l; 6 2.78 (1 H, dd, J,,, 14, J4,4a 4 Hz, exo-H-4), 3.08 (1 H, dd, J 14 and 4 Hz, endo-H-4), 5.14-5. 25 (2 H, m, H-4a and H-7), 5.36 (1 H, dd, J ,, 3 Hz, J4a,7a 9 Hz, H-7a), 6.53 (1 H, d, Js,7 3 H z , H-6), 7.30-7.50 (3 H, m), and 7.65-7.77 (2 H, m ) ; m/e 201 ( M ' ) , 183, and 103 (base).…”

Section: -( 24-dznztrophenyl) -6-(24-dinitrophenylazo)-36diphenyl-145...mentioning

confidence: 99%

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Cycloaddition reactions of nitrosoalkenes and azoalkenes with cyclopentadiene and other dienes

Faragher¹,

Gilchrist²

1979

J. Chem. Soc., Perkin Trans. 1

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“…Signals at 6 6.53 and 5.36 are assigned to the hydrogen atoms at C-6 and C-7, respectively; those at C-4a and C-7a appear as a multiplet at 6 5.14-5. 25.…”

Section: Results and Discussiionmentioning

confidence: 99%

Section: -( 24-dznztrophenyl) -6-(24-dinitrophenylazo)-36diphenyl-145...mentioning

confidence: 99%

Cycloaddition reactions of nitrosoalkenes and azoalkenes with cyclopentadiene and other dienes

Faragher¹,

Gilchrist²

1979

J. Chem. Soc., Perkin Trans. 1

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Alkendiazoniumsalze, ein neues Kapitel der klassischen Organischen Chemie

Bott

1979

Angewandte Chemie

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Professor Horst Pommer zum 60. Geburtstag gewidmetWahrend die Protonierung von a-Diazo-b-diketonen und a-Diazo-P-oxoestern rnit Chlorwasserstoff und Antimonpentachlorid Hydroxyalkendiazonium-hexachloroantimonate ergibt, konnen die ,,saureempfindlichen" a-Diazomonocarbonylverbindungen durch eine analoge O-Alkylierung mit Triethyloxonium-hexachloroantimonat in resonanzstabilisierte Alkendiazoniumsalze umgewandelt werden. Ein allgemeiner Syntheseweg zu diesen Verbindungen besteht in der Umsetzung der p-Toluolsulfonylhydrazone von a-Halogenaldehyden und a-Halogenketonen mit Lewis-Sauren. Alkendiazoniumionen ohne Mesomeriestabilisierung besitzen nur dann eine fur die Isolierung bei Raumtemperatur ausreichende thermische Stabilitat, wenn die Zersetzung bei hoherer Temperatur unter Stickstoffabspaltung zu besonders energiereichen Vinylkationen fuhrt. Kennzeichnend fur den stark elektrophilen Charakter der Alkendiazoniumsalze sind die rnit Anisol und Methanol leicht durchfuhrbaren Substitutionen an der CC-Doppelbindung. Durch elektronenspendende Substituenten an C-2 eines Ethylendiazoniumions 1aDt sich der Bindungsgrad der NN-Dreifachbindung soweit verringern, daB er dem des Diazoessigesters gleichkommt.

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Alkenediazonium Salts: A New Chapter of Classical Organic Chemistry

Bott

1979

Angew. Chem. Int. Ed. Engl.

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Whereas the protonation of a-diazo-0-diketones and r-diazo-P-oxo esters with hydrogen chloride and antimony pentachloride yields the corresponding hydroxyalkenediazonium hexachloroantimonates, the "acid-sensitive'' r-diazomonocarbonyl compounds can be transformed into resonance-stabilized alkenediazonium salts by an analogous 0-alkylation with triethyloxonium hexachloroantimonate. A general route for synthesizing these compounds consists in the transformation of the p-toluenesulfonylhydrazones of a-halogenated aldehydes and ketones with Lewis acids. Alkenediazonium ions which are not resonance stabilized can be isolated at room temperature only if their decomposition at higher temperatures leads, uia evolution of nitrogen, to vinyl cations in particularly high energy levels. Facile substitution reactions at the CC double bond with anisole and methanol demonstrate the strongly electrophilic nature of alkenediazonium salts. When electron-donating substituents are attached to C2 of an ethylenediazonium ion, the bond order of the NN triple bond can be reduced to a level comparable with that in diazoacetic ester.

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Diphenylacetylene from the decomposition of 2,2-diphenyl-1-tosylazoethylene

Cited by 11 publications

References 3 publications

Cycloaddition reactions of nitrosoalkenes and azoalkenes with cyclopentadiene and other dienes

Cycloaddition reactions of nitrosoalkenes and azoalkenes with cyclopentadiene and other dienes

Alkendiazoniumsalze, ein neues Kapitel der klassischen Organischen Chemie

Alkenediazonium Salts: A New Chapter of Classical Organic Chemistry

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